ChemInform Abstract: A Highly Stereoselective Synthesis of D-Erythrose Derivatives by One-Carbon Homologation of 2,3-O-Isopropylidene-D-glyceraldehyde with (R)-Methyl p-Tolyl Sulfoxide.

  1. Arroyo-Gomez, Y. 1
  2. Rodriguez-Amo, J. F. 1
  3. Santos-Garcia, M. 1
  4. Sanz-Tejedor, M. A. 1
  1. 1 Universidad de Valladolid

    Universidad de Valladolid

    Valladolid, España



ISSN: 0931-7597 1522-2667

Year of publication: 2010

Volume: 31

Issue: 24

Pages: no-no

Type: Article

DOI: 10.1002/CHIN.200024201 GOOGLE SCHOLAR lock_openOpen access editor

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Aldehyde (VI) is prepared in three steps with 50% overall yield via sulfoxide (III) which is obtained by the title reaction with ¿98% diastereoselectivity. Pummerer rearrangement of benzyl protected sulfoxide (Va) with (CF3-CO)2O/lutidine followed by work-up with aq. NaHCO3 gives the target compound in quantitative yield. The Pummerer rearrangement of (Va) with NaOAc/Ac2O and subsequent treatment with iBu2AlH affords aldehyde (VI) in only 60% yield. Pummerer rearrangement of (Vb) with NaOAc/Ac2O leads to an epimeric mixture of S-ketals (IX) with replacement of the Tms by the acetyl group.

Bibliographic References

  • Arroyo-Gomez, (2000), Tetrahedron: Asymmetry, 11, pp. 789, 10.1016/S0957-4166(00)00005-7